For one thing, the translator's trying way too hard with that drifting into the deep end line. I'm pretty sure a simple "We're really going in there, aren't we?" or something would sound way better.
The bunch of wh-words line (or all of them for that matter) reeks of a literal translation to me.
Anyway, I'm not even a good translator, but these lines are outright terrible and a little creativity in the English could easily make them sound way better than they are now (accuracy be damned!). Then again, I don't know the actual spoken Japanese, so this is just me talking out of my ass.